FERULIC ACID METHYL ESTER Chemical Properties

Melting point:

62-65°C

Boiling point:

163 °C(Press: 1 Torr)

Density 

1.204±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Acetone (Slightly), Chloroform (Slightly), Ethyl Acetate (Sparingly)

form 

Solid

pka

8.88±0.18(Predicted)

color 

White to Off-White

Water Solubility 

Slightly soluble in water.

InChI

InChI=1S/C11H12O4/c1-14-10-7-8(3-5-9(10)12)4-6-11(13)15-2/h3-7,12H,1-2H3

InChIKey

AUJXJFHANFIVKH-UHFFFAOYSA-N

SMILES

C(OC)(=O)C=CC1=CC=C(O)C(OC)=C1

LogP

2.209 (est)

CAS DataBase Reference

2309-07-1(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, methyl ester(2309-07-1)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RTECS 

GD9470000

HS Code 

2918999090

MSDS

• Language:English Provider:ALFA

FERULIC ACID METHYL ESTER Usage And Synthesis

Chemical Properties

It is a white crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO. It is derived from the leaves of Tetragononia tetragonoides (Pall.) O.kuntze, a member of the Aizoaceae family.

Uses

Ferulic acid is a hydroxycinnamic acid that is abundant in plants and originally derived from giant fennel (F. communis). This naturally-occurring phenolic has antioxidant activities that provide protection against inflammation and cancer. Ferulic acid methyl ester is a lipophilic derivative of ferulic acid, demonstrating increased ability to cross cell membranes. Ferulic acid methyl ester has less antioxidant capacity than ferulic acid in neuronal PC12 cells (IC50 = 74.7 μM for ferulic acid ethyl ester vs. 44.6 μM for ferulic acid, 2,2-diphenyl-1-picrylhydrazyl radical scavenging). Ferulic acid methyl ester, at 10-25 μg/ml, inhibits the release of pro-inflammatory cytokines, blocks the expression of COX-2, and reduces nitric oxide generation from LPS-stimulated macrophages.

Uses

Ferulic Acid Methyl Ester is a derivative of Ferulic Acid (F308900), used as an antioxidant and food preservative. It has less antioxidant capacity than ferulic acid.

Definition

ChEBI: A cinnamate ester that is the methyl ester of ferulic acid. It has been isolated from Pisonia aculeata.

Synthesis

General procedure for the synthesis of methyl (E)-3-(4-hydroxy-3-methoxyphenyl)acrylate from methanol and 3-methoxy-4-hydroxyphenylacrylic acid: ferulic acid (1.94 g, 10 mmol) was dissolved in anhydrous methanol (3.20 g, 100 mmol), and 0.25 mL of concentrated sulfuric acid was added as catalyst. The reaction was refluxed under stirring and the progress was monitored by thin layer chromatography (TLC). After the disappearance of the raw material point, the reaction was stopped and cooled to room temperature. The reaction mixture was poured into an ice-water system and the remaining acid was neutralized with a 10% excess of sodium carbonate solution. Subsequently, the reaction mixture was washed with saturated brine and extracted with ether. After separation of the organic phase, the organic layers were combined and dried over anhydrous sodium sulfate. After filtration to remove the desiccant, the solvent was evaporated under reduced pressure to give the crude product. The crude product was eluted with hexane and further purified by recrystallization to afford (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid methyl ester in the form of a white solid with a mass of 1.42 g (theoretical mass 2.08 g) in 68.3% yield.

References

[1] European Journal of Medicinal Chemistry, 2009, vol. 44, # 1, p. 332 - 344
[2] Chinese Chemical Letters, 2014, vol. 25, # 3, p. 474 - 478
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6085 - 6088
[4] Molecular Crystals and Liquid Crystals, 2016, vol. 624, # 1, p. 59 - 68
[5] Organic and Biomolecular Chemistry, 2009, vol. 7, # 11, p. 2367 - 2377

FERULIC ACID METHYL ESTER(2309-07-1)Related Product Information

• Milnacipran Hydrochloride
• Quinocetone
• METHYL CAFFEATE
• Methyldopa
• Arbutin
• Levobupivacaine hydrochloride
• Caffeic acid
• Resveratrol
• 2-Ethylhexyl ferulate
• Tylosin tartrate
• Hydroxychloroquine sulfate
• Hydroxytyrosol
• Ceftiofur hydrochloride
• Ethyl 4-hydroxy-3-methoxycinnamate
• Sodium ferulic
• Ferulic Acid
• Methyl cinnamate
• 3-Methoxycinnamic acid
• Methyl Ferulate